Lynn Becomes a Cuckold

Writing about a cucked cross-dresser presents unique difficulties in pronouns. I've tried to make it as clear as possible as to whom I'm describing. I cannot talk about Lynn other than she/her because I only think of her as female, so please bear with me gentle reader. Lynn and I met online, as I fully described in my previous story sets A Gentleman for Lynn and Shopping with Lynn. Ideas for our stories come from our chats. I write these for her, but you are welcome to join us!

Lynn's and my relationship was progressing nicely. Most weeks we didn't see each other, with both of us being married and my living a few hours away on the coast. But we were able to chat or talk to each other fairly frequently, a couple times a week. She would always begin our chats with a description of what kind of panties she was wearing, whether she was in chastity or not, and if she had a bra on. Lynn was a panty and undergarment cross-dresser most days and describing her "naughties" was something I had insisted on very early on in our relationship, as it helps me guide our conversations towards their eventual completion of her climaxing. We had developed a schedule, similar to married couples having sex on certain days or times, like on Sunday mornings. It wasn't ideal for sure, but it was working for us. She loved cumming during our chats, and I certainly loved taking her there.

So, I was l bit surprised by a text I received from her on one of our off days:

Call me! Lynn.

"Oh, this is not good," I thought to myself as I dialed her number. Fortunately, I was at work, and all I needed to do for privacy was to shut the door to my office. The phone rang once before she answered.

"Jim, she knows," she told me, "Teri knows everything, she found my clothes, all of them, and my toys too. Oh, what am I going to do?"

"You mean what are WE going to do, Lynn," I responded trying to be reassuring to her. She described what had happened. Lynn's wife had been doing some deep cleaning, and had stumbled on the stash of dresses, lacy undergarments, toys, lubes, and everything else Lynn had accumulated over the past several months if not years. "Oh, I knew I should have purged them, but you had bought some of them for me, so I didn't want to... Oh damn," she continued. Lynn had also come clean about us, telling Teri about our relationship, about our hooking up. "She's pretty upset," she told me.

"Has she kicked you out of the house?" I delicately asked her. "No, she still loves me she said. She said she needed some time to process all of it."

"Lynn, that is the best news yet," I told her, "Do you need me to come out?"

"No, but thanks," she replied, "and I know you mean it."

"Listen, give her time, let her think things through. We'd better stop our chats for now, but you know you can call or text me anytime, day or night, right?" I said. "You know, right?"

"I know," she said, "Oh, I knew this, our relationship, was too good to be true."

"Listen Lynnette," I addressed by her formal name, "it is NOT too good to be true. It IS good, and it IS true. You are her husband, and you love her, but you have needs too, needs that were not being fulfilled, needs that she could never meet. But I am sorry for all this."

We agreed that we would lay low and let Teri process all she had learned. I'm sure there would be some long conversations for them, and I was just hoping that I would remain a part of Lynn's life. We'd just have to see how it played out.

A week went by, and then two. This was the longest we'd gone without chatting since we met online, and I was beginning to fear the worst. First, that we'd never see each other again and second, that her marriage was irreparably harmed and that I was responsible, being the "other man." By the fourth week I had all but given up, but got a text:

Call me. All good! XXX, Lynn

"Thank God for that!" I thought as I dialed her number. She picked up straightaway.

"Lynn, sweetheart, I'm so sorry for causing all this," I began, picking up from a month earlier.

"Jim, stop. Let me explain," she replied, "It was pretty tough on her, and me, the first couple of weeks, but she came around to recognizing that if she loved me, she loved all of me. She allowed me to start wearing around the house and is getting used to it. She understands my needs, maybe even my need to suck."

"What do you mean 'understands'?"

"You're not going to believe this, but she wants to meet you."

"Yeah, so she can Bobbitize me?"

"No, not at all, so she can become a part of that part of my life too. That's the amazing thing about her! That's why I'm so excited!"

This was an amazing turn, and if it hadn't happened to us, I wouldn't have believed it either. We made plans for me to come over on Friday of the following week when she had off from work.

I drove to Charlotte that Friday morning excited to see Lynn, but with some trepidation about meeting Teri. Having been to their house before when Lynn hosted our trysts, I knew from pictures in their living room that Teri was very pretty, but I still had to play it very carefully if I wanted to keep my relationship with Lynn and not cause further damage to their marriage.

I pulled into their development and into their driveway, only a few minutes after the time we had arranged. "Well, here goes" I said to myself as I got out of the car and went up to the front door. Lynn was opening it as I did, and I had quite a surprise: she was en femme, in that silver wrap dress we had bought her a few months back. "Hello, you" I greeted her as I always did, to at least offer a semblance of normality in our relationship, one that had changed over these last few weeks. She kissed me delicately on the lips, smiled, and replied, "and hello to you, sir" as she showed me in.

There on the sofa in front of the lit fireplace was Lynn's wife. "I'm Teri," she said as she offered me her hand, "Thank you for coming over from Wilmington to talk," and then to Lynn "Would you get us some drinks, please?"

Lynn went off to the kitchen as I sat down with Teri. "I gotta say it was quite a shock when Lynn texted me last month. How did you discover us?" I asked her.

"I was doing some vacuuming -- I know, right? -- and found the box he keeps all his, what do you call it? Girlie things in. I have always teased him about his "girlish figure" and his wonderful bum, so I guess I wasn't that surprised. But still, it was a bit of a shock."

"And you accept it?" I was probing here.

"I do, Jim, because I love him, but it has altered our marriage. But I think for the good?" she was directing that question to Lynn who was coming back with some drinks for us. Lynn offered a martini to me and what looked like a G&T to her. Curiously, no drinks for herself.

"Which leads to a question of mine, Jim, which is What are YOU doing here?" She was nothing if not direct. I looked straight at Lynn as I replied to Teri, "I just wanted to set the record straight about us."

"What do you mean by that? What else is there to say?" she replied.

"Lots." I began. "And it may not mean a lot to you now, and maybe not tomorrow, but soon, and for the rest of your life, it may.

"Teri, this is all on me. I seduced Lynn. Our chats online just were not enough for me, and I couldn't stay away, so I pressed her to meet. I brought her to the Ritz-Carlton, I took her shopping and bought her expensive clothes, I led her to stray," I told her. I looked over at Lynn, who was tearing up looking back at me. She silently mouthed "Thank you."

"Well, thanks for that. Really," Teri responded. "And you enjoyed her, did you?"

"Yes. We were -- are--a good fit I think" I replied.

"Did she suck you?" she asked, "Of course she did. Is your Lynn a good cock-sucker?"

"Well, I normally wouldn't share that, but based on why I'm here, and if you really want to know, yes she is. Exquisite. What she lacks in experience she makes for in enthusiasm." I looked over at Lynn who was blushing heavily.

"Does she swallow?" she pressed on, embarrassing Lynn even further. "I want to know; does she take you in her mouth and swallow?"

"Yes of course; I insist on that." I replied honestly while still trying to play the dominant partner of the exposed relationship.

"Did you make love to her?" she continued.

"Yes of course we did."

"And she took you inside her, didn't she, to a place where not even I have been?"

"Yes."

"And why did you that, Jim, why did you make love to my husband?" She was searching for an answer that I now recognized she needed to hear.

"Because I love her." I said, looking at Lynn, who was now crying, tears dripping down her cheeks.

"Well, thank you for being so honest in admitting that. Would you further admit that we're really both here for the same reason then?" she asked.

"I believe we are, Teri, and trust me, I know that Lynn is first and foremost your devoted husband, and she, no he, doesn't want to lose you."

"Well, let's talk about that. _______ is a man. MY man in fact. MY husband, whom I have always and will always love. Could you perhaps admit that you love just a part of him? In fact, just a small part?" Teri was trying to reconcile the two relationships.

"Yes, of course I would admit that" I said, trying to satisfy her logic.

"Does your wife know about this?" she asked.

"No, not at all. Lynn and I were able to meet when she's out of town or I had business," I responded, "and I prefer to keep it that way."

"Hah, no doubt," she laughed. "I think I will use 'Lynn' too since she is clearly a woman here with us. Is that okay? Are you willing to let me into your little naughty twosome?"

"Thank you, and I think she'd like that too, isn't that so Lynn?" I asked her. I think she was somewhat, no, totally floored by what was playing out. Lynn had a secret feminine side and I have been able to draw that out, but now that her wife was a part of the secret, it was going to take getting used to. She shook her head yes.

"Lynn, aren't you forgetting something?" Teri asked her.

"No, I don't think so," she replied, "What?"

"Darling, don't you always describe to Jim what you're wearing? Why haven't you done that yet?" she asked. I could see what was occurring in their relationship.

"Um, I have black lace panties on, garter with hose, and a matching bralette." Lynn replied quietly, wiping the tears off her face.

"And what else, dear?" She was making a point.

"The cage."

"Yes, that's right. And where is the key to it?"

"Around your neck."

"That it is." Teri was clearly in charge.

"And tell Jim how long you have worn it?"

"For two weeks now"

"Good girl, Lynn. Because I just can't trust you, can I Lynn?"

"No." The sexual tension in the room was palpable. Poor Lynn was being humiliated in front of her lover but seemed to somehow be enjoying it.

Teri turned her attention back to me. "You know, she showed me the stories you write for her on the internet."

"Did she? Did you enjoy them?" I responded. It was the author in me constantly seeking affirmation.

"Yes, I did, and she pointed out to me what parts were real and what was just in your rather vivid imagination." She was clearly making a power play here with me also.

"And what did you enjoy the most?" I asked her.

"In that last story, what do you call it with her? 'Shopping Two'? I liked the part where you and Lynn's personal shopper make love," she replied, "You know, I wasn't sure what kind of man you were Jim, gay or bi until I read that part, and then I saw that you played for both teams, don't you?"

"I do, yes. I equally desire cock and clitoris. And I particularly enjoy going down on a woman, Teri," I said as I set my drink down, looked over at Lynn, and she nodded to me smiling, letting me know she was okay with everything. I leaned over on the couch, took Teri's face in my hands, and kissed her. I recognized her Jo Malone scent immediately as Lynn had borrowed it before. I wouldn't have been surprised if she had used Jennifer also as her Nordstrom's shopper also. That's how strangely this was playing out. But I wasn't going to let irony ruin a good afternoon's lovemaking.

We continued to kiss as I undid the buttons on her blouse, revealing her lace bra. Lynn's chastity key was indeed around her neck. Teri was ten years younger than I and was still a vibrant sexual being. "Lynn has told me all about you," she whispered, "how hard you get when you made love to her, when she took you inside her. Are you wearing your cock ring now? No, probably not, as you had no idea this was coming, did you?" Then to Lynn she said, "Come over here, darling and help us out of our clothes, won't you?"

Lynn did as she was bade and took off Teri's blouse all the way and unclasped her bra, exposing her magnificent breasts to me. "And him too, honey" she instructed. Lynn took my shirt off and undershirt. "Thank you, Lynn. You may remove your dress if you'd like but do leave your naughties on."

Teri must have been planning this in her mind for a while, perhaps before she outed my poor Lynn. I really didn't think on that too long as I took her nipples into my mouth and began to make love to her breasts. Lynn had told me once how nice they were, and how much the gurl in her admired them. Each woman is different, each likes her nipples teased a particular way, and it didn't take long for me to learn what Teri liked, so I just kept lightly pinching them then licking, pinching then licking, alternating nipples.

I moved down to kneel in front of her and removed her skirt. I unzipped it from the side and slid it off, exposing her already wet panties. I felt hands at my trousers. Lynn was removing my belt, unzipping the trousers and pulling them off. As I was pulling off Teri's sopping panties, Lynn was pulling off my underwear. I leaned forward to lick the newly exposed vulva as I felt Lynn's hands enveloping my now-hard member from behind me. My hands stayed on Teri's nipples, tweaking them as my tongue entered the folds of her womanhood. I wanted to give her the best cunnilingus she'd ever received, and I went at it with abandon. I concentrated on the clitoris, circling it. Then I wedged my tongue in between the clitoris and its hood and licked back and forth in that fold of sensitive skin, which got an immediate response. She put her hands on my head and directed where she wanted my tongue, moving it from the top of her clitoral hood down to her now wet rosebud. The combination of my saliva and her pussy juice was creating a literal puddle within the folds of their leather couch.

Lynn, in the meantime, was keeping herself occupied giving me indescribable pleasure. She was rimming me from behind while simultaneously playing with my cock. Her tongue was lapping back and forth across my rosebud, then it would circle it. This was pure lust - I had rimmed her before, so she knew how good it felt and was giving it to me. We stayed like that for several minutes of pleasure.

Teri was the first to break the silence between us three. "Fuck me?" she asked, a request that I wasn't about to deny. I reluctantly had to push Lynn away as I stood up to reposition in front of Teri's splayed legs. "Lynn, help him enter me," she told her. Lynn, still in her bralette and panties, held her wife's labia apart with one hand while taking my cock with the other and guided it in. It was totally unnecessary, but deliberately requested to heighten Lynn's sense of humiliation. "Ah, so this is the payback," I thought. "The ultimate cuck."

I rammed it home, plunging into her hard, even felt my cock hitting her cervix, which couldn't have felt good. That caught her by surprise, but if it hurt, she didn't show it. She looked into my eyes, urging me on. Lynn was now going at her nipples, and she was clearly loving it. "Fuck me, fuck me hard!" she demanded. I responded, raising her legs onto my shoulders and pushing harder with each thrust. I fucked her as hard as I could for as long as I could, trying to make each thrusting of my member count. "Don't stop! I'm close, I'm getting close" she cried. Lynn was now fingering her wife's clitoris as I was thrusting into her, which was putting Teri over the edge. "Ayeeeeeee," she cried out as she climaxed, "I'm cumming."

Wave after wave of her orgasm tore through her body and watching and feeling her cum triggered my own orgasm. I jetted into her, adding yet more sticky fluid to the mess dripping down her bum. Lynn moved from kissing Teri to kissing me as I came. "Mmmmmm," we both moaned into each other's mouth.

I dismounted Teri completely sated, my cock with dripping our combined juices. "Lynn," Teri nodded towards my cock, "Clean him," she told her cuckholded husband. I was able to sit down on the couch at Teri's feet.

Lynn knelt in front of me and parted my legs. Still in her bralette and panties, she began lapping up the semen and vaginal lubricants that were on my softened cock and balls.

"Look him in the eyes, Lynn," Teri told him, "Didn't he teach you that?" Lynn immediately corrected herself and looked up at me as she cleaned me. I smiled at her as lovingly as I could as she went about her task.

"That's right, girlfriend. Let me see you suck," Teri encouraged her.

Before too long, my cock was hard again from the ministrations Lynn was applying. I took her face in my hands and kissed her, tasting her lips, tasting my seed and Teri's juices.

"He's a good cocksucker, isn't he?" She asked.

"The best." I admitted. "She really is."

"Yes, well I need to be cleaned also. Lynn, can you see what he did to me?" she asked as she splayed her legs apart, exposing herself to us. Her vulva was a mess of my semen and her own juices, her pubic hair matted and almost dripping in wetness. I know I don't cum that much anymore, so she must have lubricated profusely. Lynn reluctantly left my cock and repositioned between Teri's legs and went to work. Lynn still hadn't cum, so being the always attentive lover, I repositioned behind her started kissing her bottom. I pulled her panties down to her knees and went back to kissing her bum.

She immediately responded by arching her back down, exposing her pussy like she was in heat, which of course she was. I could see the chastity cage clamped around her nutsac, and the tube holding her engorged clittie in place and downward, preventing its erection. I looked up at Teri, motioning to her to give me the key, but she shook her head no. I acknowledged this and went back to between Lynn's parted cheeks and started rimming her, licking the entire anal area, preparing it for what I was about to do. Lynn had shaved her pussy earlier in the morning and was completely smooth, hairless.

Once assured of her wetness, I knelt back up and placed the glans of my cock at the entrance to her pussy. I looked down at Teri, who was clearly enjoying the lapping Lynn was giving her and eased my way into her husband. Lynn moaned into Teri's pussy as I thrust in deeply. I knew the only way Lynn was going to cum this afternoon was hands-free from my fucking. I doubt Teri was aware of prostate milking, as it was a niche thing and perhaps not something she would have been likely to read about in women's magazines.

I started fucking Lynn with a mission. Who knew how much longer she was going to be locked up in her device, so I knew this could be the last opportunity for orgasm in a while for her, even if it meant thwarting Teri's punishment scheme. A prostate-milked orgasm wouldn't be as satisfying as my mouth would have been, but it would have to do. I put my hands on her hips and began to fuck her with abandon, trying to rub up against her prostate with every thrust of my cock. I looked down at the two in front of me, Lynn licking Teri, Teri's ample breasts bouncing with each of my pelvic thrusts into her husband, my gurl. I fucked the married couple harder and faster, going deeper into Lynn than I had ever been, occasionally reaching around to her leaking clittie for some of her pre-cum for more lubricant to slather onto my cock during its withdrawal strokes.